CN106344934A - Application of fluorescent chemicals in alpha-beta plaque imaging agents - Google Patents
Application of fluorescent chemicals in alpha-beta plaque imaging agents Download PDFInfo
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- CN106344934A CN106344934A CN201610808146.8A CN201610808146A CN106344934A CN 106344934 A CN106344934 A CN 106344934A CN 201610808146 A CN201610808146 A CN 201610808146A CN 106344934 A CN106344934 A CN 106344934A
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
The invention belongs to the field of specific molecular recognition diagnosis reagents and discloses an application of fluorescent chemicals in alpha-beta plague imaging agents. The structure of the fluorescent chemicals is as shown in the description (I). An electron-donating group and an electron-withdrawing group in the structure of the fluorescent chemicals form a conjugated structure of the push-pull electronic function, conjugated systems of transition are increased through a carbon-carbon double bond, fluorescence generated from chemical molecular moves to a near-infrared region, and the chemical molecular having appetency to alpha-beta plaques can be successfully applied to near-infrared fluorescence imaging for the alpha-beta plaques. The application has the advantages of safety without radiation, low cost, low background fluorescence interference, high penetration in biological tissue and the like.
Description
Technical field
The invention belongs to specific molecular identifying and diagnosing reagent field is and in particular to a kind of fluorescent chemicalses show in a beta plaque
As the application in preparation.
Background technology
Alzheimer's disease (alzheimer ' s disease, ad) is a kind of neurodegenerative diseases.Survey data shows
Show, in current global range, have more than 40,000,000 patients ad.And China has entered aging society in advance, investigation display China is
Have more than 8,000,000 ad patients, quantity occupies first of the world, and number of patients is with annual more than 300,000 speed increase.Ad is not only tight
Ghost image rings the disease of senior health and fitness, and brings white elephant to society and family.At present, can be clinically used for treating ad's
Medicine can not delay, terminate or reverse the development of the ad state of an illness, can only partly improve clinical symptoms.It is additionally, since the ad cause of disease multiple
Miscellaneous, definite pathogeny it is not immediately clear, is clinically mainly damaged to diagnose by evaluating the cognitive competence of patient, makes a definite diagnosis
Have been enter into the middle and advanced stage of the course of disease more patient and delay treatment.Lack effective detection meanss, it has also become ad getting up early diagnoses and controls
The major obstacles treated.
In ad patient's brain, it is the most significant pathologic mark of ad that amyloid-beta (amyloid, a β) deposits in brain
One of will.A beta plaque has started in the premorbid many decades of ad to be occurred, and is the earliest nervous tissue's degeneration mark of ad and important disease
Feature of science.In recent years, the prevention that a beta plaque is formed and reverse become one of target for the treatment of ad, and suppression a beta plaque produces in intracerebral
Life and the medicine accumulated and therapy have obtained widely studied.
In addition to ad, a beta plaque exists in other diseases, for example cerebral amyloid angiopathy, amyloid cardiomyopathy, shallow lake
Powder sample polyneuropathy, systemic senile amyloidosises and the hereditary cerebral hemorrhage with amyloidosises etc..Therefore, research and development tool
There is a beta molecule probe of specific binding a beta plaque noticeable.Carry out a beta plaque using a beta molecule probe and Molecular imaging techniques
Imaging, can achieve the tracing in vivo of noninvasive, real-time a beta plaque and detection, and then carry out early stage for Diseases such as ad and examine
Research of disconnected, examination of curative effect and medicine etc. provides great convenience.
Between the several years in past, existing more radioactivity a beta molecule probe enters clinical experimental stage, and has related pet imaging
Reagent lists, but the application of Radionuclide imaging method is also limited by some factors, and what such as radiological imaging agent was sent penetrates
Line has certain radiation damage, needs medical institutions to be configured with producing cyclotron, the radiation of radionuclide to human body
Property developer need professional and technical personnel's labelling prepare etc..Under comparing, optical imagery has the "dead", data acquisition of safety
The many advantages such as the time is short and with low cost, the application in medical diagnosiss etc. is in widespread attention in recent years.Especially closely red
Outer Imaging-PAM, because the interference of its background fluorescence is relatively low, penetration power is strong in biological tissues, and therefore, research and development have to a beta plaque
There is the near-infrared fluorescent developer (molecular probe) of affinity, will there is important scientific meaning and real value.
Content of the invention
In place of solving the shortcoming and defect of above prior art, it is an object of the invention to provide a kind of fluorescence chemical combination
Application in a beta plaque Imaging agent for the thing.
The object of the invention is achieved through the following technical solutions:
A kind of application in a beta plaque Imaging agent for fluorescent chemicalses, structure such as formula (i) institute of described fluorescent chemicalses
Show:
Application in a beta plaque localization diagnosises compositionss for the above-mentioned fluorescent chemicalses, described compositionss are included shown in formula (i)
Compound and pharmaceutically acceptable carrier.Described " pharmaceutically acceptable carrier " includes various excipient and diluent.
Pharmaceutically acceptable carrier in the composition of the present invention may include liquid, such as water, normal saline, glycerol and ethanol.
Above-mentioned fluorescent chemicalses deposit the application in the diagnostic reagent and medicine of relevant disease in a β.
Described a β deposition relevant disease refers to Alzheimer's disease or cerebral amyloid angiopathy.
The present invention provides the developing method of a beta plaque.In the first step of this developing method, by formula (i) institute of detectable amount
The compound showing is introduced in tissue or patient.Compound is typically the part of diagnosis composition and passes through those skilled in the art
Known method is administered to tissue or patient.Compound as shown in the formula (i) with detectable amount introduces patient and be enough to
After making the time that compound is combined with a beta plaque, atraumatic ground detection compound.Or the compound shown in formula (i) is introduced
Patient, through the enough time so that compound is combined with a beta plaque, takes tissue sample from patient, and departs from patient's detection tissue
Compound.Or take tissue sample from patient and the compound shown in formula (i) introduced this tissue sample.Enough to make this change
After compound is bound to the time of a beta plaque, detection compound.
Compound shown in formula (i) can be administered to by patient by overall or local route of administration.For example, it is possible to
Compound is administered to patient so that it is delivered to whole body.It is alternatively possible to compound is administered to the specific organ of concern
Or tissue.For example, in order to diagnose or follow the trail of patient ad process, need positioning and the amyloid plaques of quantitative intracerebral.
Term " patient " refers to the mankind and other animals.Those skilled in the art also know and how to determine enough to make compound
The time being combined with a beta plaque.Patient is introduced by compound shown in the formula (i) by detectable amount, then upon administration each
Detection compound at time, can be easily determined by the required time.
Term " in conjunction with " chemical interaction that refers between compound and a beta plaque.In conjunction with example include covalent bond,
Ionic bond, hydrophilic-hydrophilic interaction, hydrophobic-hydrophobic interact and complex.
Imaging means of the present invention image for optics.
With respect to prior art, the fluorescent chemicalses of the present invention are used for the imaging of a beta plaque and have the advantage that and beneficial effect
Really:
The fluorescent chemicalses of the present invention, the electron donating group in its structure and electron withdraw group define push-pull electronics and make
Conjugated structure, and increase the conjugated system of transition by carbon-carbon double bond, make the fluorescence that compound molecule produces to near-infrared
Area moves, and this compound molecule has affinity to a beta plaque simultaneously, can be used successfully to the near-infrared fluorescent imaging of a beta plaque,
Have the advantages that safety "dead", with low cost, background fluorescence interference relatively low, in biological tissues penetration power strong.
Brief description
Fig. 1 is embodiment 1 gained fluorescent chemicalses (i) probe and a β1-42Fluorescence emission spectrum before and after aggregation mixing
Figure；
Fig. 2 is that embodiment 2 gained fluorescent chemicalses (i) probe is injected after ad transgenic mice and normal mouse by tail vein
Different time points brain living imaging figure in 60min；
Fig. 3 is that embodiment 2 gained fluorescent chemicalses (i) probe is injected after ad transgenic mice and normal mouse by tail vein
The fluorescence signal figure of each time point brain；
Fig. 4 is brain after embodiment 3 gained fluorescent chemicalses (i) probe injects ad transgenic mice 30 minutes by tail vein
Section fluorescence imaging figure.
Specific embodiment
With reference to embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention do not limit
In this.
Embodiment 1
Fluorescent chemicalses (i) probe and a β1-42The vitro binding assay of aggregation:
Experimental technique: take fluorescent chemicalses (i) (according to literature method preparation: chemistry of materials, 9
(6),1437-1442；1997) it is dissolved in dimethyl sulfoxide, is configured to 10mm storing solution, be diluted to 1 μm of prepare liquid with pbs solution
(probe (i)).First record the excitation and emission spectra property of probe (i).From a β1-42Albumen is cultivated a β in 37 DEG C of water-baths and is gathered
Collective, for simulating a β protein masses in human brain.By probe (i) and a β1-42(5 μm) mixing of aggregation, application fluorescence divides
Light photometer carries out fluoroscopic examination.
The present embodiment middle probe (i) and a β1-42Fluorescence spectra before and after aggregation mixing is shown in Fig. 1.Can be seen by Fig. 1
Go out, the fluorescent chemicalses (i) of the present invention maximum emission wavelength in pbs is 680nm, has reached near infrared region.Fluorescence chemical combination
After thing (i) is combined with a beta peptide aggregation body, blue shift in launch wavelength, and maximum emission wavelength is 635nm.Fluorescent chemicalses (i)
With a β1-42The mixed fluorescence intensity of aggregation significantly strengthens, and is 12 times of compound autofluorescence intensity.
Embodiment 2
Fluorescent chemicalses (i) probe application is in ad transgenic mice living imaging:
Experimental procedure: by fluorescent chemicalses (i) solution probe (4mg/kg, 10% Tween 80,20%dmso, 70%pbs)
Ad transgenic mice (tg, app/ps1 are double to be turned, 10 monthly ages) and normal mouse (wt, c57bl6,10 monthly age) are entered by tail vein injection
In vivo, carry out mouse species image collection in 10min, 30min, 60min respectively under the continuous narcosis of Isoflurane
(caliper life science, ivis luminaxr, excitation wavelength takes 500nm, and launch wavelength takes 635nm and 680nm),
Analysis result.Imaging results analysis is carried out using living imaging software.
The imaging experiment result of the present embodiment is as shown in Figures 2 and 3.Result shows, fluorescent chemicalses (i) can pass through blood
Brain barrier, the fluorescence signal of brain reached peak value at 10 minutes about.10 minutes afterwards, the brain fluorescence letter of ad transgenic mice
Number intensity is better than normal mouse.Clearance rate (10min/60min=in ad transgenic mice body for the fluorescent chemicalses (i)
1.76) obvious normal mouse (10min/60min=2.78) to be slower than, shows that probe is combined with a beta plaque of mice intracerebral rear stagnant
Stay mouse brain, make the fluorescence signal of ad mouse brain apparently higher than normal mouse it is adaptable to the fluorescence imaging of live body.
Embodiment 3
Fluorescent chemicalses (i) probe application fluorescence staining in ad transgenic mice body
Experimental procedure: the ad transgenic mice (app/ps1 is double to be turned) used by animal scanning in embodiment 2 is raised 15 days,
Allow probe in its thoroughly metabolism in vivo.By fluorescent chemicalses (i) solution probe (4mg/kg, 10% Tween 80,20%dmso,
70%pbs) ad transgenic mice (11 monthly age) is entered in vivo by tail vein injection, after 30 minutes, disconnected neck is put to death, rapid taking-up brain group
Knit, be placed in -20 DEG C of freezing 20-30 minutes after being embedded with oct mixing embedding medium (1:1) with 20g/l sucrose, then cut into slices
(10μm).Slice, after drying at room temperature, is placed in fluorescence microscopy Microscopic observation, takes pictures, result is as shown in fig. 4 a.Identical is cut into slices
Dyeed (0.3%, water: ethanol=1:1) with thioflavin s, equally with fluorescence microscope, taken pictures, result such as Fig. 4 b institute
Show.Shown by Fig. 4 a and 4b result, fluorescent chemicalses (i) clearly can be dyeed with a beta plaque of mice intracerebral；Use sulfur
The counterstaining (Fig. 4 b) that plain s is carried out can be very good to overlap with the speckle of compound dyeing, further illustrates our probe
In ad mouse brain internal labeling is a beta plaque.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention are not subject to above-described embodiment
Limit, other any spirit without departing from the present invention and the change made under principle, modification, replacement, combine, simplify,
All should be equivalent substitute mode, be included within protection scope of the present invention.
Claims (4)
1. a kind of fluorescent chemicalses in a beta plaque Imaging agent application it is characterised in that the structure of described fluorescent chemicalses such as
Shown in formula (i):
2. a kind of application in a beta plaque Imaging agent for the fluorescent chemicalses according to claim 1 it is characterised in that: institute
State fluorescent chemicalses to be used for preparing a beta plaque localization diagnosises compositionss, described compositionss include the compound shown in formula (i) and medicine
Acceptable carrier on.
3. a kind of application in a beta plaque Imaging agent for the fluorescent chemicalses according to claim 1 it is characterised in that: institute
State diagnostic reagent and the medicine that fluorescent chemicalses deposit relevant disease for preparing a β.
4. a kind of application in a beta plaque Imaging agent for the fluorescent chemicalses according to claim 3 it is characterised in that: institute
The a β deposition relevant disease stated refers to Alzheimer's disease or cerebral amyloid angiopathy.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610808146.8A CN106344934A (en) | 2016-09-07 | 2016-09-07 | Application of fluorescent chemicals in alpha-beta plaque imaging agents |
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| CN201610808146.8A CN106344934A (en) | 2016-09-07 | 2016-09-07 | Application of fluorescent chemicals in alpha-beta plaque imaging agents |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108061725A (en) * | 2017-02-16 | 2018-05-22 | 昆明医科大学 | Application of the 1,8- naphthyridines base fluorescent molecular probes in ketamine amusement sexual abuse neuromechanism research and the diagnosis of habituation degree |
| CN115340511A (en) * | 2021-05-13 | 2022-11-15 | 中国科学院大连化学物理研究所 | Fluorescent compound, preparation method thereof and application of fluorescent compound as fluorescent probe |
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|---|---|---|---|---|
| CN1283665A (en) * | 2000-08-31 | 2001-02-14 | 山东大学 | Red fluorescent materials for electroluminescent device and its preparing process |
| CN104178132A (en) * | 2014-07-30 | 2014-12-03 | 四川大学 | Fluorescent compound and application thereof in medicine |
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2016
- 2016-09-07 CN CN201610808146.8A patent/CN106344934A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1283665A (en) * | 2000-08-31 | 2001-02-14 | 山东大学 | Red fluorescent materials for electroluminescent device and its preparing process |
| CN104178132A (en) * | 2014-07-30 | 2014-12-03 | 四川大学 | Fluorescent compound and application thereof in medicine |
Non-Patent Citations (1)
| Title |
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| XU ZHANG ET AL.: "Synthesis and fluorescence of dicyanoisophorone derivatives", 《DYES AND PIGMENTS》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108061725A (en) * | 2017-02-16 | 2018-05-22 | 昆明医科大学 | Application of the 1,8- naphthyridines base fluorescent molecular probes in ketamine amusement sexual abuse neuromechanism research and the diagnosis of habituation degree |
| CN115340511A (en) * | 2021-05-13 | 2022-11-15 | 中国科学院大连化学物理研究所 | Fluorescent compound, preparation method thereof and application of fluorescent compound as fluorescent probe |
| CN115340511B (en) * | 2021-05-13 | 2023-10-31 | 中国科学院大连化学物理研究所 | Fluorescent compound, preparation method thereof and application of fluorescent compound as fluorescent probe |
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